I'm looking to learn more about the various agreements that exist between countries; agreements that state what city-pairs a route can operate, what airlines are allowed to operate it, what aircraft (if this is applicable), and so on and so forth ...

Specifically, I'm interested in those agreements affecting North America, and even more specifically Canada (although others are welcomed as more general information). I could probably stumble around Google looking this stuff up but I figured I'd go straight to the experts right here.

I keep reading about "bermuda"-this "fifth freedom"-that and and "open skies"-such and such and am pretty much totally stupid in this area. Help!

A good thing to read if you want to understand the international framework of civil aviation regulation, i.e. the system of the treaties and agreements, I could recommend you to read parts I and II of An Introduction to Air Law by I.H.Ph. Diederiks-Verschoor, available at most university libraries. You'll get the idea on why the legal framework exists in the first place, and it will give you a nice historical overview.

"Get your facts first. Then you may distort them as much as you please" -- Mark Twain